New water-soluble carbonates from beta-tribromoethylalcohol



Patented Sept. 9, 1930 warren stares.

earns? j JQFFICE JtrnsEN cameras, or ELBERFELD, GERMANY, A'ssrsnoa ro-winrrrnon CHEMICAL COMPANY, Inc, or new Yon-K, n. Y;,-.A'con-roaarron or YORK NEW WATER-SOLUBLE cARBonA'rEs mom. s-FIQRIB ROMOETHYLALCOHOL No Drawing. AppIication filed April 15, 1829, Serial No. 3 5 5,, 4 23,ani1 in Germany ApriI 28,1928.

The present invention relates to new watersoluble carbonates from fl-tribromoethylalcowherein R means an alkylene group (CH --C H and the like) and R and R stand for alkyl groups, can be transformed into other salts, for instance by dissolving the s-ame in water, liberating the base by the addition of an alkali and reacting upon the free base with a suitable organic less crystals, soluble in water and alcohol,

nearly insoluble in ether and exerting valuable narcotic properties. Especially the hy- .rochloric acid salts of the compounds of the probable formula:

wherein R means the methylor ethyl group,

were found to be valuable media for rectal anesthesia.

Compared with B-tribromoethylalcohol as rectal anesthetic, they have the great advantage of being easily soluble in water without decomposition, whereas the former is diffi-' cul-tly soluble in cold water and decomposes,

when heating its aqueous solution.

The followingbxample illustrates my invention, without limiting it thereto, the parts being by weight:

Ewample.34 5.5 parts of tribromoethyl-. chlorocarbonate -(colorless liquid boiling at 103 C(at api'essure of 10 mm, being obtainable by reactingupon ,8 trib'romoethylalcohol with phosgene in'the presence of di methylaniline. in the usual manner) are dissolved in 5000 parts of benzene.

are'add'ed, while cooling. 1 The reaction product soon begins toseparate in a crystalline form. After some hours the reaction mixture is filtered and the residue is recrystallized from hot alcohol. The hydrochloric acid salt of tribromoethyldimethylaminoethylcarbonate of the probable formula:

thus obtainable forms colorless crystals, melting at 184 C., easily soluble in water and more diflicultly soluble in hot alcohol. The compound can be transformed into other salts, for instance, by liberating the base by means of potassium carbonate and adding hydrobromic acid, acetic acid or the like, or

also by double decomposition, for instance with silver nitrate, whereby a well crystallizing nitric acid salt of the base is formed.

When replacing in the above example the dilnethylaminoethanol by another alkylaminoalcohol, for instance diethylaminoethanol, compounds of similar properties will be obtained.

I claim:

1. As new products salts of-the compounds of the probable general formula:

wherein R means an alkylene group, R and R stand for alkylgroups, said products forming colorless crystals, soluble in water To this solution 89 parts of dimethylaminoethanol Ill and alcohol, nearly insoluble in ether, and exerting valuable narcotic properties.

2. As new products the hydrochloric acid salts of the compounds of the probable general formula /R1 O.R| N'\R2 wherein R means an alkylene group, R and R stand for alkyl groups, said products forming colorless crystals, soluble in Water and alcohol, nearly insoluble in ether, and exerting valuable narcotic properties.

3. As new products the hydrochloric acid salts of the compounds of the probable general formula:

wherein R means the methylor ethyl group, said products forming colorless crystals, easily soluble in Water, more diflicultly soluble in hot alcohol, and exerting valuable narcotic properties.

In testimony whereof I have hereunto set my hand.

JURGEN CALLSEN. 

